Nitration of Phenoxathiin and Some New Amino Derivatives<sup>1</sup>

Nobis, John F.; Blardinelli, Albert J.; Blaney, Donald J.

doi:10.1021/ja01110a025

Cited by 18 publications

(2 citation statements)

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“…The studied diamine monomers, SSDA, SODA, and OODA, were prepared based on previous reports − with some modification of the synthetic procedure. The synthetic scheme and structural characterization (including 1 H and 13 C NMR) of synthesized reagents and diamines are shown in the Supporting Information (SI) (Scheme S1 and Figures S1 and S2).…”

Section: Methodsmentioning

confidence: 99%

Thermally and Mechanically Stable Polyimides as Flexible Substrates for Organic Field-Effect Transistors

Chen

Lin

Miyane

et al. 2020

ACS Appl. Polym. Mater.

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Highly thermal-mechanical stable polymers have attracted extensive research interest as substrates for flexible or wearable electronic devices, such as polyimides (PIs). Here, we report a class of PIs as substrates for flexible organic field-effect transistors (OFETs), prepared by the polycondensation of pyromellitic dianhydride (PMDA) or 3,3′,4,4′-biphenyltetracarboxylic acid dianhydride (BPDA) with three kinds of heterocyclic diamines, including 2,6-diaminothianthrene (SSDA), 2,6-diaminophenoxathiin (SODA), and 2,6-diaminodibenzo-p-dioxin (OODA). Flexible and tough PI films were obtained with a very low coefficient of thermal expansion (CTE) down to 7.3 ppm K −1 . Furthermore, the copolymers of PI(OODA−PmBn) prepared from PMDA and BPDA with OODA could exhibit an extremely low CTE of 5.5 ppm K −1 (PI(OODA−P5B5)) without an observed T g up to 400 °C, which was attributed to the suitable polymer chain rigidity and packing resulting in better in-plane orientation. Finally, this superheat-resistant PI(OODA−P5B5) was applied as the substrate in flexible OFETs, showing compatible and stable device performance even after being baked at 200 °C for 2 h or bended for 1000 cycles. These results indicate that the designed super-thermal-mechanically stable polyimides have potential applications as substrates for flexible electronics.

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Section: Methodsmentioning

confidence: 99%

Thermally and Mechanically Stable Polyimides as Flexible Substrates for Organic Field-Effect Transistors

Chen

Lin

Miyane

et al. 2020

ACS Appl. Polym. Mater.

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“…2,8-Dinitrophenoxatiin 10,lO'-dioxide was prepared by nitration and simultaneous oxidation of phenoxatiin by the method described by Nobis et a1. 10 The catalytic reduction of the dinitro compound on Raney nickel produced 2,8-diaminophenoxatiin 10,lO'-dioxide in high yield.…”

Section: Monomersmentioning

confidence: 99%

Heat‐resistant polymers with thianthrene analog units. II . Aromatic polyamides

Niume

Nakamichi

Toda

et al. 1980

J. Polym. Sci. Polym. Chem. Ed.

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A series of polyamides which contained thianthrene, phenoxatiin, and dibenzo‐p‐dioxin units was synthesized from tricyclic fused‐ring diamines and aromatic diacid chlorides by solution polycondensations at a low temperature. The amorphous polyisophthalamides were highly soluble in polar organic solvents, whereas some of the polyterephthalamides with a fair degree of crystallinity were insoluble. The solubility of the series of polyamides increased in the order of the dibenzo‐p‐dioxin‐containing polymers < phenoxatiin‐containing polymers < thianthrene‐containing polymers. The thermal stability increased in the reverse order and the dibenzo‐p‐dioxinpolyamides were more thermostable than the corresponding open‐chain polymers with diphenyl ether linkages. The polyamides derived from 2,8‐oriented tricyclic diamines showed somewhat lower glass transition temperatures than those from 2,7‐oriented diamines.

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TheBeckmann Rearrangement

Donaruma

Heldt

2011

Organic Reactions

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The rearrangement of a ketoxime to the corresponding amide was discovered in 1886 by E. Beckmann and is known as the Beckmann rearrangement. The rearrangement is brought about by acids, including Lewis acids. The more common rearranging agents are concentrated sulfuric acid, phosphorus pentachloride in ether, and Beckmann's mixture, hydrogen chloride in a mixture of acetic acid and acetic anhydride. The Beckmann rearrangement is used frequently to determine the structure of ketones, by identification of the acid and amine obtained by hydrolysis of the amide formed by the rearrangement. There is no uniform convention for the designation of the stereochemistry of oximes in the literature. The conventions used in this chapter for the configurations of ketoximes and aldoximes are explained.

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Nitration of Phenoxathiin and Some New Amino Derivatives¹

Cited by 18 publications

References 0 publications

Thermally and Mechanically Stable Polyimides as Flexible Substrates for Organic Field-Effect Transistors

Thermally and Mechanically Stable Polyimides as Flexible Substrates for Organic Field-Effect Transistors

Heat‐resistant polymers with thianthrene analog units. II . Aromatic polyamides

TheBeckmann Rearrangement

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Nitration of Phenoxathiin and Some New Amino Derivatives1

Cited by 18 publications

References 0 publications

Thermally and Mechanically Stable Polyimides as Flexible Substrates for Organic Field-Effect Transistors

Thermally and Mechanically Stable Polyimides as Flexible Substrates for Organic Field-Effect Transistors

Heat‐resistant polymers with thianthrene analog units. II . Aromatic polyamides

TheBeckmann Rearrangement

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Nitration of Phenoxathiin and Some New Amino Derivatives¹